9S-acyloxy cinchonine derivatives, preparation method and application thereof, and plant-derived insecticide

A technology of acyloxy cinchonines and derivatives, which is applied in the field of botanical insecticides, can solve problems such as unreported research, and achieve the effects of simple operation, mild reaction conditions, and good insecticidal effect

Active Publication Date: 2020-02-07
HENAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the research on cinchonine is mainly concentrated in the field of asymmetric synthesis and chiral catalysis, and there is no report on the insecticidal aspects of cinchonine and cinchonine derivatives

Method used

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  • 9S-acyloxy cinchonine derivatives, preparation method and application thereof, and plant-derived insecticide
  • 9S-acyloxy cinchonine derivatives, preparation method and application thereof, and plant-derived insecticide
  • 9S-acyloxy cinchonine derivatives, preparation method and application thereof, and plant-derived insecticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0049] This embodiment is the preparation method of compound 3a in embodiment 1, specifically comprising the following steps:

[0050] (1) Weigh 0.5mmol of cinchonine (1), 0.6mmol of glacial acetic acid (2a), 0.6mmol of DCC and 0.1mmol of DMAP in a 50mL flask and mix well, then add 10mL of calcium hydride dried Dichloromethane, react at room temperature after mixing evenly, adopt TLC tracking detection in the reaction process, the reaction ends after the raw material reaction is complete;

[0051](2) Then remove urea by filtration to obtain the filtrate; the filtrate is diluted with 40 mL of dichloromethane, and then the diluted solution is sequentially washed with 0.1mol / L hydrochloric acid (25 mL), saturated sodium bicarbonate solution (25 mL) and saturated Brine (25mL) was washed successively, and then dried with anhydrous sodium sulfate; the dried dilution was distilled off under reduced pressure to remove the solvent to obtain a solid, and then the solid was separated by ...

Embodiment 15

[0057] This example is the preparation method of compound 3b, specifically refer to the preparation process of Example 14, the only difference is: replace glacial acetic acid (2a) with n-hexanoic acid (2b), the reaction involved is:

[0058]

[0059] The yield of compound 3b prepared by the preparation method of this example was 39%. Carry out 400MHz proton nuclear magnetic resonance spectrum test to the obtained compound 3b, the solvent that adopts during the test is CDCl 3 , TMS is the internal standard, and the test results are as follows figure 2 Shown, the specific chemical shift δ of each peak is: 8.88 (d, J=4.4Hz, 1H), 8.22 (dd, J=8.8Hz, 1.2Hz, 1H), 8.13 (dd, J=8.4Hz, 1.2Hz , 1H), 7.69-7.73(m, 1H), 7.57-7.61(m, 1H), 7.38(d, J=4.4Hz, 1H), 6.56(d, J=7.2Hz, 1H), 5.98-6.07( m, 1H), 5.07-5.13(m, 2H), 3.33(q, J=8.4Hz, 1H), 2.85-2.95(m, 2H), 2.65-2.80(m, 2H), 2.32-2.41(m, 2H), 2.22-2.29(m, 1H), 1.80-1.85(m, 2H), 1.51-1.58(m, 3H), 1.19-1.29(m, 4H), 0.89-0.98(m, 2H), 0.86...

Embodiment 16

[0062] This example is the preparation method of compound 3c, specifically refer to the preparation process of Example 14, the only difference is: replace glacial acetic acid (2a) with benzoic acid (2c), the reaction involved is:

[0063]

[0064] The yield of compound 3c prepared by the preparation method of this example was 54%. Carry out 400MHz proton nuclear magnetic resonance spectrum test to the obtained compound 3c, the solvent that adopts during the test is CDCl 3 , TMS is the internal standard, and the test results are as follows image 3 Shown, the specific chemical shift δ of each peak is: 8.87 (d, J=4.4Hz, 1H), 8.32 (dd, J=8.4Hz, 1.2Hz, 1H), 8.08-8.14 (m, 3H), 7.70- 7.74(m, 1H), 7.57-7.65(m, 2H), 7.44-7.48(m, 3H), 6.80(d, J=7.2Hz, 1H), 5.98-6.07(m, 1H), 5.06-5.13( m, 2H), 3.48(q, J=8.4Hz, 1H), 2.90-3.03(m, 2H), 2.68-2.85(m, 2H), 2.25-2.32(m, 1H), 1.94-2.01(m, 1H), 1.85-1.87 (m, 1H), 1.56-1.69 (m, 3H).

[0065] The high resolution chromatography (HRMS, ESI) t...

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Abstract

The invention belongs to the technical field of heterocyclic compounds, particularly relates to 9S-acyloxy cinchonine derivatives and a preparation method and application thereof, and further relatesto a plant-derived insecticide. A structural formula of the 9S-acyloxy cinchonine derivatives is as follows: (please see the specification for the formula), wherein R is selected from any one of an alkyl, a phenyl alkylene, a naphthyl alkylene, a phenyl and a substituted phenyl; the number of carbon atoms in the alkyl is 1 to 5; the number of carbon atoms of an alkylene in each of the phenyl alkylene and the naphthyl alkylene is 1 to 4; and a substituted group in the substituted phenyl is one or more of a halogen, a nitryl, an alkoxy, and an alkyl with 1 to 4 carbon atoms, and the number of carbon atoms in the alkoxy is 1 to 3. The 9S-acyloxy cinchonine derivatives have good insecticidal activity, the insecticidal effects of most of derivatives exceed commercialized plant-derived insecticide, namely toosendanin, the 9S-acyloxy cinchonine derivatives have good application prospects, and a new direction is provided for development of plant-derived pesticides.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to a 9S-acyloxy cinchonine derivative, a preparation method and application thereof, and a botanical insecticide. Background technique [0002] Studies have shown that the roots and stems of C.calisaya are toxic to melon silk borer (Diaphaniahyalinata L.) and diamondback moth (Plutellaxylostella L.); (TineapellionellaL.) has repellent effect; the stem bark of red cinchona tree (C.pubescens) can also repel moths (Xu Hanhong, Insecticidal Plants and Botanical Insecticides, China Agricultural Press, Beijing: 2000, 49-50 ). Therefore, cinchona should have active ingredients that can kill or repel insects. Existing studies have shown that quinine in cinchona has certain insecticidal activity ("Research Progress on Quinine Compounds", Che Zhiping, Chemical Bulletin , 2018, 81(9):792-796). [0003] Cinchonine is one of the secondary metabolites of cinchona tree...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/04A01N43/90A01P7/04
CPCA01N43/90C07D453/04
Inventor 车志平田月娥夏彦飞刘圣明陈根强林晓民孙迪杨进明
Owner HENAN UNIV OF SCI & TECH
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